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In one sense, job seeking is worse because you need a job in order to have a decent standard of living. If you fuck up a date, the worst that happens is that you're unhappy about it. If you fuck up a job interview, you still feel bad but there is also still pressure on you to keep finding more interviews to go to until you get a job.

In another sense, job seeking is easier because there's (usually) more clarity involved. You know what they are looking for, you know the set of skills and experience that you have, and you get to inform potential employers directly about them. You pretty much know up front whether you have the abilities needed to do a job, but it's hard to know up front whether you will be compatible with someone for a relationship.